.omega.-Aryl-inter-phenylene-9-deoxy PGD.sub.1 compounds
Prostaglandin analogs with the following cyclopentane ring structure: ##STR1## are disclosed along with intermediates useful in their preparation and processes for their preparation. These analogs are useful for some of the same pharmacological purposes as the prostaglandins, particularly and especially as blood platelet aggregation inhibitors.
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The present invention relates to prostaglandin analogs for which the essential material constituting a disclosure therefor is incorporated by reference here from U.S. Pat. No. 4,099,014.
Claims
1. A prostaglandin analog of the formula ##STR2## WHEREIN D is ##STR3## wherein Y is cis--CH.dbd.CH--, trans--CH.dbd.CH--, or --CH.sub.2 CH.sub.2 --;
- wherein Z.sub.6 is ##STR4## WHEREIN G IS ONE, 2, OR 3; WHEREIN M.sub.1 is ##STR5## wherein R.sub.5 and R.sub.6 are hydrogen or methyl, with the proviso that one of R.sub.5 and R.sub.6 is methyl only when the other is hydrogen;
- Wherein L.sub.1 is ##STR6## wherein R.sub.3 and R.sub.4 are hydrogen, methyl, or fluoro, being the same or different, with the proviso that one of R.sub.3 and R.sub.4 is hydrogen or fluoro only when the outer is hydrogen or fluoro;
- wherein Z.sub.3 is oxa or methylene;
- wherein T is chloro, fluoro, trifluoromethyl, alkyl of one to 3 carbon atoms, inclusive, or alkoxy of one to 3 carbon atoms, inclusive, and s is zero, one, 2, or 3, the various T's being the same or different, with the proviso that more than two T's are other than alkyl, with the further proviso that Z.sub.3 is oxa only when R.sub.3 and R.sub.4 are hydrogen or methyl, being the same or different; and
- wherein R.sub.1 is hydrogen, alkyl of one to 12 carbon atoms, inclusive, cycloalkyl of 3 to 10 carbon atoms, inclusive, cycloalkyl of 3 to 10 carbon atoms, inclusive, aralkyl of 7 to 12 carbon atoms, inclusive, phenyl, phenyl substituted with one, two, or three chloro or alkyl of one to 3 carbon atoms, inclusive, or a pharmacologically acceptable cation;
- with the further proviso that D is ##STR7## only when Y is --CH.sub.2 CH.sub.2 --.
2. A compound according to claim 1, wherein M.sub.1 is ##STR8##
3. A compound according to claim 1, wherein M.sub.1 is ##STR9##
4. A compound according to claim 3, wherein D is ##STR10## and Y is --CH.sub.2 CH.sub.2 --.
5. A compound according to claim 4, wherein Z.sub.3 is methylene.
6. A compound according to claim 5, wherein s is zero or one and T is chloro, fluoro, or trifluoromethyl.
7. A compound according to claim 6, wherein g is one.
8. A compound according to claim 7, wherein R.sub.5 and R.sub.6 are both hydrogen.
9. A compound according to claim 8, wherein R.sub.3 and R.sub.4 are both hydrogen.
10. 3,7-In ter-m-phenylene-17-phenyl-4,5,6,18,19,20-hexanor-13,14-dihydro-9,10-didehyd ro-9-deoxy-PGD.sub.1, a compound according to claim 9.
11. A compound according to claim 4, wherein Z.sub.3 is oxa.
12. A compound according to claim 11, wherein s is zero or one and T is chloro, fluoro, or trifluoromethyl.
13. A compound according to claim 3, wherein D is ##STR11##
14. A compound according to claim 13, wherein Z.sub.3 is methylene.
15. A compound according to claim 14, wherein s is zero or one and T is chloro, fluoro, or trifluoromethyl.
16. A compound according to claim 15, wherein g is one.
17. A compound according to claim 16, wherein R.sub.5 and R.sub.6 are both hydrogen.
18. A compound according to claim 17, wherein R.sub.3 and R.sub.4 are both nydrogen.
19. 3,7-In ter-m-phenylene-17-phenyl-4,5,6,18,19,20-hexanor-9-deoxy-PGD.sub.1, a compound according to claim 18.
20. A compound according to claim 13, wherein Z.sub.3 is oxa.
21. A compound according to claim 20, wherein s is zero or one and T is chloro, fluoro, or trifluoromethyl.
22. A compound according to claim 21, wherein g is one.
23. A compound according to claim 22, wherein R.sub.5 and R.sub.6 are both hydrogen.
24. A compound according to claim 23, wherein R.sub.3 and R.sub.4 are both hydrogen.
25. 3,7-In ter-m-phenylene-16-phenoxy-4,5,6,17,18,19,20-heptanor-9-deoxy-PGD.sub.1, a compound according to claim 24.
- derwent Abstract, 690955-B, BE766009-Q, 10-20-71. Derwent Abstract, 48794Y/28, BE850-204, 07-07-77. Chem. Abstr., 86:43269n, Kunstmann, R., 02-09-76. Chem. Abstr., 86:120868m, Skuballe, 28-10-76.
Type: Grant
Filed: May 8, 1978
Date of Patent: Sep 18, 1979
Assignee: The Upjohn Company (Kalamazoo, MI)
Inventor: David C. Peterson (Portage, MI)
Primary Examiner: Paul J. Killos
Attorney: Robert A. Armitage
Application Number: 5/903,626
International Classification: C07C17700;
